


Try Something New

by mushiemadarame



Series: Teen Wolf fics from Tumblr [2]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Drabble, Exploration, First Time, Male Solo, Masturbation, Other
Language: English
Status: Completed
Published: 2019-02-21
Updated: 2019-02-21
Packaged: 2019-11-02 00:11:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 938
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17877437
Author URL: https://archiveofourown.org/users/mushiemadarame/pseuds/mushiemadarame
Summary: On the rare time off, Derek finally tries something he's been curious about since he was a teenager.





	Try Something New

One fateful day, Derek discovers that he likes things up his ass.

He’s not sure how it started. One or twice, when he’d let himself think about it, Derek had considered he could be bisexual. He’s never really thought too hard about it, his life is too frantic and there’s no time for sexual crises between all the running away from danger and blood. 

But he has always been curious, he was a teenager too, after all. He thinks back to when he found a threesome video this one time, with two guys and a girl, and maybe the two guys were really enjoying each other’s company, maybe even more than it’s usually portrayed in a threesome with a girl. 

In the end, he didn’t have enough time to dwell on it, his home gone and his family turning into a bad memory soon after that.

But Derek is not a teenager anymore, and he’s too tired to care about crises, he just wants to enjoy the little time he has for himself. That little thing itching is still at the back of his mind, though, that image of the guy who was really enjoying those two fingers up his ass in that one porn video when he was 16.

At first, he’s not so sure. The whole concept doesn’t exactly resonate as a pleasurable one in his head; and, yes, he does know how his anatomy works and that his prostate is supposed to feel really good, but that’s only in theory, right?

Then, one day, he’s kind of bored, alone in the small apartment he finally bought when the thought of living where Boyd died became unbearable. It’s been so long since he’s had enough time to just enjoy himself, he thinks, and the memory randomly pops up in his head again. Why not? He could try, it’s not like he’s got anything to lose.

So he lies back on his comfy creamy couch, still fully clothed, and goes slow, so painfully slow. 

He softly caresses his neck and torso through the burgundy t-shirt he’s wearing, delicately but firmly pressing against his nipples and sliding down, down, down, oh so slowly, just above the waistband of his jeans. He lifts his shirt a tiny bit, carefully stroking his happy trail, eyes closed and mind peaceful.

He lifts his t-shirt up under his armpits in one swift movement, gets to work on his nipples again, a little stronger, but still only teasing. He goes from one to the other, pressing harder and harder against them each time, the nubs perking up, standing out from his smooth skin. When the soft noises start spilling from his lips, his hand reaches down and pops open the button of his jeans where the bulge of his hardening cock is already starting to press against the zipper and pulls that down too. The other arm, cushioning his head until that moment, takes the place working his nipples to continue teasing them, while he strokes the bulge peeking out of the V of his open pants thought the fabric of his underwear, moans growing a little steadier and louder.

Finally, he just decides to go for it. He sits up and discards first his shirt and then his pants and boxers in a quick but graceful movement, his muscles poised a tight with anticipation

Naked, he lies back down and takes his cock in the ring of his right hand, the left slowly working at his balls. He sets a slow and tight rhythm, determined to make it last long enough to try. While he keeps stroking his hard cock, he spreads his legs, lifting one to the back of the couch, and lowers the hand that was caressing his ballsack, only teasing his perineum at first, slipping a finger between his cheeks soon after, and circling his hole.

Suddenly, he’s feeling a little insecure. He shakes his head, chasing away the feeling, and moans loudly when he finally presses his middle finger against his asshole, the awareness of what he’s about to do making his cock leak pre-come on his thumb. He pushes deeper, presses on slowly and clumsily wiggles around with the digit, a little awkward and not really sure about what he’s doing. It doesn’t really feel bad, just weird, just different.

He keeps moving his finger thoughtlessly, ready to give up already until something finally goes off. He can feel it, pleasure shooting up his spine as he opens his mouth in a breathless “Oh”, eyes open wide in wonder. He chases the feeling frantically, trying to do it again, finally succeeds and keeps going until the inside of his head goes white. The only thought that manages to make its way into his brain is that he needs more of that pressure.    
He tries adding another finger, takes a little more to get used to the wider stretch around them both. Eventually, he can move the fingers in a slow stroke inside himself, looking for that spot, and it feels like fucking heaven.

He can’t stop, he keeps going and going, grips his cock tighter and faster without even noticing, brushing the tip with his thumb with every upstroke, moans spilling steadily and noisily from his mouth.

He finally feels the muscles in his abdomen clench and comes so hard that it hits his throat. Gingerly, he takes his fingers out, right hand still caressing his cock through the aftershocks, breath panting heavily, relaxation pervading every inch of his body.

And that is when he decides that he might just start understanding the appeal of sex toys.


End file.
